Visible-Light-Driven Multicomponent Reactions of Diazosulfonium Triflates with Amines and CS₂ or CO₂: Direct Synthesis of Bis-Dithiocarbamates/Carbamates

Abstract

Visible light-induced transformation of CO₂ and CS₂ into value-added products has attracted worldwide attention because it mimics nature. In this context, although visible-light-induced direct synthesis of dithiocarbamates and carbamates employing SO₂ and CO₂ as a C1 source has been reported, all these reactions are limited to the preparation of S-alkyl mono-dithiocarbamates and O-alkyl mono-carbamates. Herein, we report a visible-light photoredox-catalyzed multicomponent reaction of diazosulfonium triflates with amines and CS₂ or CO₂. Mechanistic studies indicate that the diazomethyl radicals might be generated as the key intermediates, thus providing a direction for the application of diazomethyl radicals with other radical acceptors.

Keywords

Photocatalytic / α-Diazosulfonium triflates / Diazomethyl radical / O-Alkyl di-carbamates / S-Alkyl di-dithiocarbamates / Radicals / Synthetic methods / Cross-coupling

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